Water → 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-6-ene

HRID 337841

反応式

HRID 337841 の反応式
I[C:2]1[C:3]2([CH2:8][CH2:9][CH2:10][CH:11]=1)[O:7][CH2:6][CH2:5][O:4]2.C([Li])CCC.[CH3:17][C:18]1([CH3:29])[C:22]([CH3:24])([CH3:23])[O:21][B:20](OC(C)C)[O:19]1.O>C1COCC1>[CH3:17][C:18]1([CH3:29])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([C:2]2[C:3]3([CH2:8][CH2:9][CH2:10][CH:11]=2)[O:7][CH2:6][CH2:5][O:4]3)[O:19]1

参加物

6

反応物 4

HCID 962WaterHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 146318076-Iodo-1,4-dioxaspiro[4.5]dec-6-eneHCID 178418339Butyllithium

生成物 1

HCID 899634516-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-6-ene収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 6-iodo-1,4-dioxaspiro[4.5]dec-6-ene (Synlett, 2008, 1086-1090; 2.70 g, 10.2 mmol) in THF (30 mL), butyl lithium (1.65 M solution in hexane; 6.7 mL, 11.1 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 1 hour. Then, 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (4.0 mL, 19.8 mmol) was added thereto, and the mixture was stirred at −78° C. for 2 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1) to yield the title compound (1.52 g, 56%) as a colorless oil.

後処理

  1. stirringthe mixture was stirred at −78° C. for 2 hours
  2. extractionfollowed by extraction with ethyl acetate (50 mL)
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-beb2518ec90842ddbc94d74f4d5a8283
出典データセット
uspto-grants-2014_11
特許番号
US08889741B2

関連ノート

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